Upcoming Events

For Mother's Day, celebrate the amazing women who deserve to be pampered! Show your love by gifting them an unforgettable experience at Inn at Perry Cabin, where every moment is wrapped in luxury.

Hop into Perry Cabin this Easter for a brunch celebration like no other! Join us for a delightful feast with Easter egg hunts alongside the beloved Easter Bunny. Gather your family and friends for a day of joy, delicious food, and cherished memories.

Save the date for the upcoming Eastern Shore Sea Glass and Coastal Arts Festival, taking place on Saturday, April 12th and Sunday, April 13th at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. This Spring Edition promises an extraordinary showcase of coastal craftsmanship, with over 90 exhibitors presenting a diverse collection of jewelry, home décor, art, and more.

Rain, Rain, Go Away… We’re Paws-ing ‘til a Brighter Day!  Due to the forecast,  Paws & Plates has been rescheduled to Wednesday, June 18. Same location, same pup-approved fun!

Join us for Paws & Plates, a dog-friendly evening at the Lighthouse on the Pointe, welcoming locals and visitors alike from 4 to 7 pm. Bring your pup and enjoy live music, our pizza oven, and a wine and beer bar, all while supporting a great cause: 10% of proceeds will benefit Talbot Humane Society. Don’t miss the doggie menu and pop-up shop filled with treats and toys for your four-legged friend!

Mark your calendars for August 10th as the Chesapeake Bay Maritime Museum comes to life with the Waterman’s Appreciation Day & Crab Feast. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat! Visit here to read about the history and importance of the Chesapeake Bay Watermen. 

Celebrate Memorial Day weekend with us! Start Friday with live music on the Waterside Lawn from 3 to 6 PM. On Saturday, enjoy an elevated poolside experience with a special menu by The Botanist, available from 12 to 3 PM. Then on Sunday, head waterside from 11:30 AM to 2:30 PM for live music, grilled favorites, our pizza oven, and wine cart!

Rain, Rain, Go Away… We’re Paws-ing ‘til a Brighter Day!  Due to the forecast,  Paws & Plates has been rescheduled to Wednesday, June 18. Same location, same pup-approved fun!

Join us for Paws & Plates, a dog-friendly evening at the Lighthouse on the Pointe, welcoming locals and visitors alike from 4 to 7 pm. Bring your pup and enjoy live music, our pizza oven, and a wine and beer bar, all while supporting a great cause: 10% of proceeds will benefit Talbot Humane Society. Don’t miss the doggie menu and pop-up shop filled with treats and toys for your four-legged friend!

Plan ahead for the 37th Antique & Classic Boat Festival at the Chesapeake Bay Maritime Museum, happening June 13–15! Enhance your experience with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat. Visit here for event details and highlights.

Slide into the spirit of summer with us on Fridays, June 13, and 27, and Saturday, June 21, from 3–6 PM. Partake in sun-drenched afternoons with live music, sweeping waterfront views, tasty bites, and crisp, refreshing beverages. The carefree rhythm of summer starts now!

Join us every Wednesday from 5:30–7:00 PM through August 27 for an evening of sailing, storytelling, and handcrafted tastings from our friends at LYON Rum . This adventure is timed perfectly to catch a front-row view of the Wednesday Night Sailboat Races on the Miles River.  Visit our Fleet page to learn more!

Join us for a star-spangled celebration with the best seats in town! Settle into our cozy waterfront Adirondack chairs—or take to the water aboard one of our elegant vessels—for a truly unforgettable view of St. Michaels’ dazzling fireworks display.

July 5th Fireworks Cruise:
Group Charter | 8–10 PM | $185 per person
*Charters include bubbly and sweet treats. Tax and gratuity additional. 

Plein Air Easton, celebrating its 21st year July 11 - 20 2025, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.